Perfectly situated in the heart of Woodstock Village, this charming move-in-ready single-level country cottage offers comfort, character, and flexibility just moments from the town's renowned restaurants, galleries, boutiques, markets, music venues, and year-round attractions. The home features two spacious bedrooms, each with walk-in closets, random-width pegged hardwood floors, recessed lighting, ceiling fans, custom built-in entertainment center, and updated windows with removable grilles. The inviting living room is centered around a wood-burning fireplace, creating a warm and welcoming atmosphere. The eat-in kitchen showcases shaker-style knotty pine cabinetry, a farmhouse sink, all-new appliances, and a convenient laundry area. A true highlight is the stunning three-season screened porch with vaulted A-frame ceilings, floor-to-ceiling screens, and a built-in entertainment center--perfect for relaxing or entertaining while enjoying views of the beautifully landscaped grounds. Outside, discover mature gardens, a tranquil pond, Zen garden, charming fencing, gravel pathways, and a private patio ideal for outdoor dining and gatherings. The attractive novelty siding exterior adds to the home's timeless Woodstock appeal. Additional features include a whole-house generator servicing both the main residence and the permitted studio cottage, a fully waterproofed crawl space with excellent storage, a two-car carport, and a private driveway accommodating up to five vehicles. The separate permitted studio cottage (STR) offers outstanding flexibility as a guest space, home office, artist studio, creative retreat, or potential income opportunity. Whether you're seeking a full-time residence, weekend getaway, or downsizing opportunity, this special Woodstock property combines location, charm, functionality, and move-in-ready condition in one of the Hudson Valley's most desirable village settings.